Sam,
I was sure I would never pass but got to the point where I didn't care. Attitude is important, because if you are anxious and driving yourself crazy worrying about whether you pass or not, you won't.
I would go out very early in the morning sometimes but I never went out at night unless I was with others. There are a lot of creepy people who come out from under their rocks at night. Plus, a number of them have some alcohol or other substance in their system by then.
When I went full-time, I had a woman's haircut, a little makeup, and fake breasts. I wore women's jeans and top – nothing too girly. I carried a workaday purse and wore earrings and a small pendant. I probably looked like I had the day before in man-monde but with the breasts. As everyone, including me, got used to me walking around that way I became more openly female.
The hard thing about going from the closet to the street is that there is a lot to learn. If you can ease your way into it somehow, you can learn as you go.
And friends are a wonderful resource.
Good luck, Sam.

- Kate